Acetic Acid → 6-Chloromethyl-1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene

HRID 364761

反応式

HRID 364761 の反応式
[CH3:1][O:2][C:3]1[C:12]2[C:11]([CH3:14])([CH3:13])[CH2:10][CH2:9][C:8]([CH3:16])([CH3:15])[C:7]=2[CH:6]=[C:5]([CH3:17])[CH:4]=1.C(O)(=O)C.P(=O)(O)(O)O.[ClH:27].[CH2:28]=O>C1C=CC=CC=1>[Cl:27][CH2:28][C:4]1[C:5]([CH3:17])=[CH:6][C:7]2[C:8]([CH3:16])([CH3:15])[CH2:9][CH2:10][C:11]([CH3:13])([CH3:14])[C:12]=2[C:3]=1[O:2][CH3:1]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1004Phosphoric AcidHCID 2267025-Methoxy-1,1,4,4,7-pentamethyl-1,2,3,4-tetrahydronaphthalene

生成物 1

HCID 190951706-Chloromethyl-1,1,4,4,7-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

反応条件

温度
95 °C

実験手順

1-Methoxy-3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene (23.2 g, 0.1 mol), prepared according to Example 2, was added to a stirred solution of acetic acid (18.2 g, 0.3 mol), 85% phosphoric acid (17.6 g, 0.15 mol), hydrochloric acid (28.7 g, 0.3 mol) and paraformaldehyde (7.3 g, 0.24 mol). The mixture was stirred and heated at 95° C. for 16 h. The reaction mixture was then cooled to 25° C., benzene (50 mL) added, and stirred vigorously. The organic layer was separated, washed with water (2×25 mL), neutralized with 5% sodium bicarbonate solution, and dried (Na2SO4). The solvent was removed by distillation to provide 2-chloromethyl-1-methoxy-3,5,5,8,8,-pentamethyl-5,6,7,8-tetrahydronaphthalene, GLC purity 84%.

後処理

  1. temperatureThe reaction mixture was then cooled to 25° C.
  2. stirringstirred vigorously
  3. customThe organic layer was separated
  4. washwashed with water (2×25 mL)
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed by distillation

出典と根拠

ORDレコード
ord-c8687e61aa3448abbd6716af3118ebc1
出典データセット
uspto-grants-1986_08
特許番号
US04605778

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