p-Toluenesulfonic acid → HCID 20206192, compound

HRID 543314Notes

Reaction equation

HRID 543314 reaction equation
[C:1]([C:4]1[C:10]([OH:11])=[CH:9][CH:8]=[CH:7][C:5]=1[OH:6])(=[O:3])[CH3:2].[CH3:12][C:13](=[CH2:21])[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:1]([C:4]1[C:5]([OH:6])=[C:7]([C:13]([CH3:21])([CH3:12])[CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:8]=[CH:9][C:10]=1[OH:11])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 696872',6'-DihydroxyacetophenoneHCID 642298methyl 5-methylhex-5-enoate

Product 1

HCID 20206192HCID 20206192, compound

Conditions

Temperature
100 °C

Procedure

1.5 Parts of 2-acetyl resorcinol, 1.4 parts of methyl 5-methyl-hex-5-enoate, and 0.1 parts of p-toluene sulphonic acid are sealed into a glass Carius tube and maintained at 100° C. for 48 hours. The reaction mixture is then washed free of the acid catalyst and chromatographed through silica to yield methyl 5-(3'-acetyl-2,4-dihydroxyphenyl)-5-methyl-hexanoate with m.p. 94°-7° after crystallisation from 40°-60° C. petroleum-ether.

Workup

  1. washThe reaction mixture is then washed free of the acid catalyst
  2. customchromatographed through silica

Sources & evidence

ORD record
ord-785a0df30d334d80ad6c48a7761bc98b
Source dataset
uspto-grants-1987_04
Patent number
US04661601

Reaction notes

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