Water → Dimethyl 4-[3-(3-ethyl-4-hydroxyphenyl)propyl]phthalate

HRID 970834Notes

Reaction equation

HRID 970834 reaction equation
C(OC[O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[C:18](=[CH:23][CH:24]=2)[C:19]([O:21][CH3:22])=[O:20])=[CH:8][C:7]=1[CH2:29][CH3:30])C.S(=O)(=O)(O)O.O>CO>[CH2:29]([C:7]1[CH:8]=[C:9]([CH2:12][CH2:13][CH2:14][C:15]2[CH:16]=[C:17]([C:25]([O:27][CH3:28])=[O:26])[C:18](=[CH:23][CH:24]=2)[C:19]([O:21][CH3:22])=[O:20])[CH:10]=[CH:11][C:6]=1[OH:5])[CH3:30]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 17983048Dimethyl 4-[3-(4-ethoxymethoxy-3-ethylphenyl)propyl]phthalate

Product 1

HCID 17983037Dimethyl 4-[3-(3-ethyl-4-hydroxyphenyl)propyl]phthalate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.9 g (16.6 mmol) of dimethyl 4-[3-(4-ethoxymethoxy-3-ethylphenyl)propyl]phthalate are dissolved in 100 ml of methanol. 3 ml of concentrated sulphuric acid are added dropwise, and the medium is stirred fro 1 hour, and then poured into water, and extracted with dichloromethane. The organic phases are dried and concentrated. The residue obtained is purified by chromatography on a silica column (eluent heptane 80/ethyl acetate 20). A colorless oil is obtained (m=5 g, y=84%).

Workup

  1. extractionextracted with dichloromethane
  2. customThe organic phases are dried
  3. concentrationconcentrated
  4. customThe residue obtained
  5. customis purified by chromatography on a silica column (eluent heptane 80/ethyl acetate 20)
  6. customA colorless oil is obtained (m=5 g, y=84%)

Sources & evidence

ORD record
ord-48a5a14a1de2424ba378568e7d3ac337
Source dataset
uspto-grants-2007_12
Patent number
US07312249B2

Reaction notes

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