3-Hydroxybenzyl alcohol → 2-(3-Hydroxymethylphenoxy)phenylacetic acid

HRID 129594

반응식

HRID 129594 반응식
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].C(=O)([O-])[O-].[K+].[K+].Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([OH:26])=[O:25].Cl>O.CN(C=O)C>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH2:23][C:24]([OH:26])=[O:25]

참가 물질

7

반응물 4

HCID 1023-Hydroxybenzyl alcoholHCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 877542-Bromophenylacetic acid

생성물 1

HCID 151257372-(3-Hydroxymethylphenoxy)phenylacetic acid수율 130.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

3-Hydroxybenzyl alcohol (31.0 g) was ground finely and stirred with potassium carbonate (34.6 g), 2-bromophenylacetic acid (26.9 g) and cuprous chloride (large spatula full) under nitrogen. The mixture was warmed to 140° C., and stirred vigorously for 31/2 hours. DMF (60 ml) was then added to the stirred melt and the solution was allowed to cool, poured into water and acidified with dilute hydrochloric acid. The aqueous layer was extracted with ether, and the ether extracts were washed with water, dried and evaporated to give 2-(3-hydroxymethylphenoxy)phenylacetic acid as a brown oil (42.03 g) which was used without further purification.

후처리

  1. temperatureto cool
  2. extractionThe aqueous layer was extracted with ether
  3. washthe ether extracts were washed with water
  4. customdried
  5. customevaporated

출처 및 근거

ORD 기록
ord-ccde36f6580d4ba39e2922e675ab5822
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05468857

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